from the University of Warwick

CH264 - Organic Chemistry II

Module content and teaching

Principal aims

This module builds on first year organic chemistry, using the three-dimensional shapes of molecules (a ground state effect) to begin to understand their influence upon chemical reactivity (a transition state effect). It lays the foundations for understanding many organic reactions and the mechanisms by which they take place. Stereochemistry is of crucial importance in understanding how molecules interact with, or are part of, biological systems. We learn to use hybrid molecular orbitals to predict shapes and reactivity of aliphatic, alicyclic and saturated heterocyclic molecules. Extending this approach to aromatic systems, module aims also include illustrating both the electrophilic and nucleophilic substitution reactions of benzene. The effects of ring substituents on these reactions will also be discussed in detail. The concept of aromaticity is further developed by examining the effect of incorporating heteroatoms into aromatic systems and the study broadened to look at the synthesis and reactivity of aliphatic heterocyclic compounds.

Principal learning outcomes

By the end of the module the student should be able to: Assign C-I-P (R/S) nomenclature to a range of stereogenic centres including non-carbon centres; Be able to competently draw a range of three-dimensional molecules in two dimensions and appreciate key stereochemical conventions; Appreciate that stereochemistry is not necessarily associated with a stereogenic centre. Give examples of helically and axially chiral molecules; Be able to carry out conformational analysis of simple acyclic and cyclic molecules using appropriate diagrams (Newman projections, chair / boat structures); Explain the effect of ring size on energy and conformation of small and medium sized rings; Explain in mechanistic terms how conformation in cyclic systems directly affects reactions such as base catalysed (E2) eliminations in cyclic systems; Appreciate importance of enantio- and diastereotopism; Understanding of the mechanistic concept to describe chemical reactions and awareness of some of the tools to derive mechanistic insight; Construction of a reaction profile based on kinetic and thermochemical properties of a chemical reaction; Confident design of labelling experiments to obtain mechanistic insight into the reaction; Understanding of the concept of kinetic isotope effects and its use to determine energetic and geometrical changes; Differentiate the ring substituents on benzene into activating and deactivating, and ortho/para or meta directing; Understand the role hetero atoms play in the chemistry of heteroaromatic systems; Understand how & when to use organopalladium chemistry in heterocyclic synthesis; Describe the synthesis and chemistry of aliphatic heterocyclic compounds; Understand how & when to use organopalladium chemistry in heterocyclic synthesis.